In the 1950s, most motorists relied on paper maps to navigate long drives. These maps showed two routes: red routes, or main roads, and blue routes, or backroads. While many blue routes were poor-quality roads, the maps did not always reflect that. Using one such paper map from a gas station, Annie plotted a route northward to Missouri and then west across Kansas. Her route made sense on paper but meant that she would not access major towns for a long time as she passed through the rural Ozarks region.

This area had experienced economic booms due to logging operations before experiencing the devastating environmental consequences of this extractive industry and further declining during the Great Depression. During the 1950s, the state marketed the Ozarks as an ideal tourist destination because of its picturesque river park, a trend that the remaining residents resisted, wanting to preserve their rural, traditional lifestyle. Like the rest of the US, this region was increasingly developed for vehicle traffic. This shift rendered foot and horse travel obsolete, so people like Annie were an unusual exception to the new car culture. Among the first towns on her route, Marshfield, Missouri, warmly welcomed her and her animals and treated her to a luncheon and gifts.